#------------------------------------------------------------------------------
#$Date: 2019-12-26 20:49:47 +0200 (Thu, 26 Dec 2019) $
#$Revision: 246080 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/16/2311678.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2311678
loop_
_publ_author_name
'Carletta, Andrea'
'Tilborg, Anaëlle'
'Moineaux, Laurence'
'de Ruyck, Jérôme'
'Basile, Livia'
'Salerno, Loredana'
'Romeo, Giuseppe'
'Wouters, Johan'
'Guccione, Salvatore'
_publ_section_title
;
 How does binding of imidazole-based inhibitors to heme oxygenase-1
 influence their conformation? Insights combining crystal structures and
 molecular modelling.
;
_journal_issue                   'Pt 4'
_journal_name_full
'Acta crystallographica Section B, Structural science, crystal engineering and materials'
_journal_page_first              447
_journal_page_last               454
_journal_paper_doi               10.1107/S2052520615010410
_journal_volume                  71
_journal_year                    2015
_chemical_formula_moiety         'C11 H9 Br N2 O'
_chemical_formula_sum            'C11 H9 Br N2 O'
_chemical_formula_weight         265.10
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.1389(7)
_cell_length_b                   7.5691(5)
_cell_length_c                   27.0498(15)
_cell_measurement_reflns_used    2524
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.1328
_cell_measurement_theta_min      3.3520
_cell_volume                     2075.9(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3712
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_sigmaI/netI    0.0284
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            7194
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         3.44
_exptl_absorpt_coefficient_mu    3.932
_exptl_absorpt_correction_T_max  0.822
_exptl_absorpt_correction_T_min  0.692
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.696
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle-like
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.267
_refine_ls_extinction_coef       0.0030(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1821
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0323
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0367P)²+0.6352P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0710
_refine_ls_wR_factor_ref         0.0759
_reflns_number_gt                1505
_reflns_number_total             1826
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            lo5002sup1.cif
_cod_data_source_block           1b
_cod_database_code               2311678
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
C C1 0.9710(3) 0.3077(4) 0.53886(10) 0.0416(7) Uani d . 1 1
H H1 1.0442 0.3774 0.5319 0.050 Uiso calc R 1 1
C C2 0.8099(3) 0.1211(3) 0.52966(10) 0.0394(7) Uani d . 1 1
H H2 0.7503 0.0401 0.5166 0.047 Uiso calc R 1 1
C C3 0.8128(3) 0.1835(4) 0.57615(10) 0.0445(7) Uani d . 1 1
H H3 0.7544 0.1506 0.6010 0.053 Uiso calc R 1 1
C C4 0.9478(3) 0.1782(4) 0.45398(9) 0.0357(6) Uani d . 1 1
H H4A 0.9439 0.0535 0.4459 0.043 Uiso calc R 1 1
H H4B 1.0381 0.2172 0.4492 0.043 Uiso calc R 1 1
C C5 0.8589(3) 0.2791(3) 0.41889(9) 0.0324(6) Uani d . 1 1
C C6 0.8756(2) 0.2468(3) 0.36502(9) 0.0305(6) Uani d . 1 1
C C7 0.7789(3) 0.3063(4) 0.33305(10) 0.0395(7) Uani d . 1 1
H H7 0.7066 0.3674 0.3455 0.047 Uiso calc R 1 1
C C8 0.7887(3) 0.2760(4) 0.28289(10) 0.0411(7) Uani d . 1 1
H H8 0.7230 0.3159 0.2616 0.049 Uiso calc R 1 1
C C9 0.8958(3) 0.1869(3) 0.26456(9) 0.0357(6) Uani d . 1 1
C C10 0.9941(3) 0.1265(3) 0.29573(10) 0.0386(7) Uani d . 1 1
H H10 1.0666 0.0667 0.2830 0.046 Uiso calc R 1 1
C C11 0.9835(3) 0.1559(3) 0.34578(10) 0.0355(6) Uani d . 1 1
H H11 1.0490 0.1148 0.3669 0.043 Uiso calc R 1 1
N N1 0.9126(2) 0.2011(3) 0.50543(8) 0.0339(5) Uani d . 1 1
N N2 0.9137(2) 0.3022(4) 0.58199(9) 0.0495(7) Uani d . 1 1
O O1 0.7774(2) 0.3806(3) 0.43462(7) 0.0522(6) Uani d . 1 1
Br Br1 0.90954(3) 0.14638(4) 0.195554(10) 0.04969(16) Uani d . 1 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N2 C1 N1 112.7(3)
N2 C1 H1 123.7
N1 C1 H1 123.7
C3 C2 N1 106.0(3)
C3 C2 H2 127.0
N1 C2 H2 127.0
C2 C3 N2 110.8(3)
C2 C3 H3 124.6
N2 C3 H3 124.6
N1 C4 C5 113.3(2)
N1 C4 H4A 108.9
C5 C4 H4A 108.9
N1 C4 H4B 108.9
C5 C4 H4B 108.9
H4A C4 H4B 107.7
O1 C5 C6 121.9(2)
O1 C5 C4 120.5(2)
C6 C5 C4 117.6(2)
C7 C6 C11 119.0(2)
C7 C6 C5 118.6(2)
C11 C6 C5 122.4(2)
C8 C7 C6 120.7(2)
C8 C7 H7 119.7
C6 C7 H7 119.7
C9 C8 C7 119.6(2)
C9 C8 H8 120.2
C7 C8 H8 120.2
C8 C9 C10 120.8(2)
C8 C9 Br1 119.5(2)
C10 C9 Br1 119.6(2)
C11 C10 C9 119.4(3)
C11 C10 H10 120.3
C9 C10 H10 120.3
C10 C11 C6 120.5(2)
C10 C11 H11 119.7
C6 C11 H11 119.7
C1 N1 C2 106.1(2)
C1 N1 C4 127.5(2)
C2 N1 C4 126.4(2)
C1 N2 C3 104.5(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N2 1.304(4)
C1 N1 1.349(3)
C1 H1 0.9300
C2 C3 1.344(4)
C2 N1 1.372(3)
C2 H2 0.9300
C3 N2 1.371(4)
C3 H3 0.9300
C4 N1 1.447(3)
C4 C5 1.516(4)
C4 H4A 0.9700
C4 H4B 0.9700
C5 O1 1.205(3)
C5 C6 1.487(3)
C6 C7 1.382(3)
C6 C11 1.394(4)
C7 C8 1.379(4)
C7 H7 0.9300
C8 C9 1.372(4)
C8 H8 0.9300
C9 C10 1.382(4)
C9 Br1 1.897(3)
C10 C11 1.376(4)
C10 H10 0.9300
C11 H11 0.9300
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
N1 C2 C3 N2 0.6(3)
N1 C4 C5 O1 7.1(4)
N1 C4 C5 C6 -172.4(2)
O1 C5 C6 C7 -13.2(4)
C4 C5 C6 C7 166.3(2)
O1 C5 C6 C11 168.0(3)
C4 C5 C6 C11 -12.4(4)
C11 C6 C7 C8 0.2(4)
C5 C6 C7 C8 -178.6(2)
C6 C7 C8 C9 -0.4(4)
C7 C8 C9 C10 0.2(4)
C7 C8 C9 Br1 -179.7(2)
C8 C9 C10 C11 0.3(4)
Br1 C9 C10 C11 -179.86(19)
C9 C10 C11 C6 -0.5(4)
C7 C6 C11 C10 0.3(4)
C5 C6 C11 C10 179.0(2)
N2 C1 N1 C2 -0.2(3)
N2 C1 N1 C4 178.2(2)
C3 C2 N1 C1 -0.2(3)
C3 C2 N1 C4 -178.7(2)
C5 C4 N1 C1 -101.0(3)
C5 C4 N1 C2 77.1(3)
N1 C1 N2 C3 0.6(3)
C2 C3 N2 C1 -0.7(3)
